IVAS 2022 banner
IVES 9 IVES Conference Series 9 IVAS 9 IVAS 2022 9 Hemisynthesis, NMR Characterization and UHPLC-Q-Orbitrap /MS² identification of (+)-Catechin oxidation products in red wines and grape seed extracts

Hemisynthesis, NMR Characterization and UHPLC-Q-Orbitrap /MS² identification of (+)-Catechin oxidation products in red wines and grape seed extracts

Abstract

(+)-Catechin—laccase oxidation dimeric standards were hemi-synthesized using laccase from Trametes versicolor in a water-ethanol solution at pH 3.6. Eight fractions corresponding to eight potential oxidation dimeric products were detected. The fractions profiles were compared with profiles obtained with two other oxidoreductases: polyphenoloxidase extracted from grapes and laccase from Botrytis cinerea. The profiles were very similar, although some minor differences suggested possible dissimilarities in the reactivity of these enzymes. Five fractions were then isolated and analyzed by 1D and 2D NMR spectroscopy. The addition of traces of cadmium nitrate in the samples solubilized in acetone-d6 led to fully resolved NMR signals of phenolic protons, allowing the unambiguous structural determination of six reaction products, one of the fractions containing two enantiomers. These products were then analyzed in grape seed extracts and red wines (UHPLC-Q-Orbitrap MS). The different dimers had different fragmentation patterns according to their interflavan linkage position. Oxidation dimeric compounds had a specific fragment ion at m/z 393, missing for B-Type dimers fragmentations. A fragment ion at m/z 291 occurred and was specific for oxidation dimeric compounds with a C-O-C linkage. Higher level oxidation products had abundant specific fragments: m/z 425, 397 and 245. These fragmentations were useful to identify them in complex samples such as grape seed extracts and wines. Three grape varieties and three ripening stages were selected and the corresponding seed extracts were obtained. The analyses revealed an increasing trend for the oxidation markers during grape ripening. The analysis of Syrah wines (2018, 2014, 2010) showed a decreasing trend of these molecules during wine ageing which might be due to further oxidation.

DOI:

Publication date: June 23, 2022

Issue: IVAS 2022

Type: Article

Authors

Saucier Cedric1, Deshaies Stacy1, Le Guernevé Christine1,2, Sommerer Nicolas1,2, Garcia Lucas Suc François1, Mouls Laetitia1

1SPO, Université de Montpellier, INRAE, Institut Agro, UMR SPO, Faculté de Pharmacie, 15 avenue Charles Flahault, 34000 Montpellier, France
2INRAE, PROBE Research Infrastructure, PFP Polyphenol Facility, 34060 Montpellier, France

Contact the author

Keywords

wine, grape, polyphenol,oxidation, catechin

Tags

IVAS 2022 | IVES Conference Series

Citation

Related articles…

Différenciation mésoclimatique des terroirs alsaciens et relation avec les paramètres du milieu naturel

The influence of climatic conditions on the development of the vine and on the quality of the wines no longer needs to be demonstrated at the scale of the vineyard, by the regional climatic characteristics, determining on this scale the viticultural potentialities (Huglin, 1978; Branas, 1946; Riou et al ., 1994); but also on a local scale, at the level of the basic terroir unit (Morlat, 1989), by the landscape differentiation of the natural environment inducing climatic variability within the same vineyard, and partly explaining differences in functioning of the vine, in connection with the processes of maturation and the quality of the wine (Becker, 1977 and 1984; Morlat, 1989 and Lebon, 1993a). According to these authors, the climatic diversity in a wine region constitutes in addition to the edaphic component, an important component of characterization of the Basic Terroir Units (UTB).

EFFECTS OF WINEMAKING FACTORS AND AGEING ON THE POLYPHENOLIC AND COLORIMETRIC PROFILES IN RED WINES PRONE TO COLOUR INSTABILITY

The effects of (A) grape freezing, and (B) malolactic fermentation, have been evaluated on the chemical and colorimetric profiles of red wines from Schiava grossa cv. grapes, thus prone to colour instability. The aim was to observe if specific variables (e.g. grape freezing) could improve the extraction and stability of pigments. The samples were studied from musts up to twelve months in bottle. The study was conducted with independent parallel micro-vinifications (12 = 4 theses x 3 replicates) under strictly-controlled conditions.

Metabolomic study of mixed Saccharomyces cerevisiae yeast during fermentation

Alcoholic fermentation conducted by microorganism is a key step in the production of wine. In this process, interactions between different species of yeast are widely described but their mechanisms are still poorly understood. The interactions studied in wine are mainly between Saccharomyces and non-Saccharomyces species. Therefore, little is known about the mechanisms of interactions

An automated cooling system to mitigate thermal and radiative stresses in Pignoletto white grapes

In the context of increasingly hot and dry summers, the adoption of innovative irrigation technologies has become essential for maintaining grape production while minimizing water use.

Grapevine sugar concentration model in the Douro Superior, Portugal

Increasingly warm and dry climate conditions are challenging the viticulture and winemaking sector. Digital technologies and crop modelling bear the promise to provide practical answers to those challenges. As viticultural activities strongly depend on harvest date, its early prediction is particularly important, since the success of winemaking practices largely depends upon this key event, which should be based on an accurate and advanced plan of the annual cycle. Herein, we demonstrate the creation of modelling tools to assess grape ripeness, through sugar concentration monitoring. The study area, the Portuguese Côa valley wine region, represents an important terroir in the “Douro Superior” subregion. Two varieties (cv. Touriga Nacional and Touriga Franca) grown in five locations across the Côa Region were considered. Sugar accumulation in grapes, with concentrations between 170 and 230 g l-1, was used from 2014 to 2020 as an indicator of technological maturity conditioned by meteorological factors. The climatic time series were retrieved from the EU Copernicus Service, while sugar data were collected by a non-profit organization, ADVID, and by Sogrape, a leading wine company. The software for calibrating and validating this model framework was the Phenology Modeling Platform (PMP), version 5.5, using Sigmoid and growing degree-day (GDD) models for predictions. The performance was assessed through two metrics: Roots Mean Square Error (RMSE) and efficiency coefficient (EFF), while validation was undertaken using leave-one-out cross-validation. Our findings demonstrate that sugar content is mainly dependent on temperature and air humidity. The models achieved a performance of 0.65